9-Oxononyl 2-[diethoxy(oxido)phosphaniumyl]acetate | 1218919-59-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 9-Oxononyl 2-[diethoxy(oxido)phosphaniumyl]acetate
• 英文别名: 9-oxononyl 2-[diethoxy(oxido)phosphaniumyl]acetate
• CAS: 1218919-59-5
• 化学式: C₁₅H₂₉O₆P
• 分子量: 336.365
• InChiKey: IDCVKJYIOBBVFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 9-Oxononyl 2-[diethoxy(oxido)phosphaniumyl]acetate
  参考文献：
  名称：

  Z-Selective Intramolecular Horner−Wadsworth−Emmons Reaction for the Synthesis of Macrocyclic Lactones

  摘要：

  When the substrates (ArO)(2)P(O)CH2CO2-CHO (Ar = Ph, o-t-BuPh) were added to a THF solution containing 3 equiv of NaH at 0 degrees C or NaI-DBU at rt over 1-10 h, the Intramolecular Horner-Wadsworth-Emmons reaction proceeded efficiently to give the 12-18-membered-ring lactones in 69-93% yields with 89-100% Z selectivity. On the other hand, (EtO)(2)P(O)CH2CO2-CHO gave the 13-18-membered-ring lactones in 52-82% yields with 89-99% E selectivity using LiCl-DBU in MeCN or THF.

  DOI：

  10.1021/ol100071d

文献信息

• <i>Z</i>-Selective Intramolecular Horner−Wadsworth−Emmons Reaction for the Synthesis of Macrocyclic Lactones
  作者：Kaori Ando、Kenji Narumiya、Hirokazu Takada、Taiji Teruya

  DOI：10.1021/ol100071d

  日期：2010.4.2

  When the substrates (ArO)(2)P(O)CH2CO2-CHO (Ar = Ph, o-t-BuPh) were added to a THF solution containing 3 equiv of NaH at 0 degrees C or NaI-DBU at rt over 1-10 h, the Intramolecular Horner-Wadsworth-Emmons reaction proceeded efficiently to give the 12-18-membered-ring lactones in 69-93% yields with 89-100% Z selectivity. On the other hand, (EtO)(2)P(O)CH2CO2-CHO gave the 13-18-membered-ring lactones in 52-82% yields with 89-99% E selectivity using LiCl-DBU in MeCN or THF.